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Asymmetric Synthesis of Concentricolide
Author(s) -
Liu Xiaojing,
Hu Lingling,
Jiang Lizhen,
Jia Junhao,
Zhang Di,
Chen Xiaochuan
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403604
Subject(s) - chemistry , oxazoline , aldehyde , combinatorial chemistry , condensation , stereochemistry , organic chemistry , catalysis , physics , thermodynamics
A practical strategy for the synthesis of both (–)‐ and (+)‐concentricolide from salicylic acid has been developed. The key feature of the approach is sequential aromatic lithiation and condensation with an aldehyde directed by a chiral oxazoline unit derived either from L ‐ or D ‐phenylalaninol, which is employed as an auxiliary.